Key West is the end of Route 1 and the end of the United States: after driving for hours over bridges with turquoise sea on both sides, you reach a small island of wooden houses with porches, roosters roaming the streets and six-toed cats. You can get around the whole place on foot or by bike, and its old town keeps the mix of seafaring past, Cuban influence and bohemian spirit that drew Hemingway, Tennessee Williams and Truman.
The day plans itself: small, well-kept museums in the morning, the southernmost point buoy before the queue builds, a lazy beach break at Fort Zachary Taylor and, as the sun goes down, Mallory Square, where people gather every evening to applaud the sunset among jugglers and musicians. At night, Duval Street turns into a corridor of bars with live music. If you love the sea, the coral reef is just minutes away by boat.
The star excursion is a long way out: Dry Tortugas National Park, a 19th-century brick fort in the middle of the sea, about 113 km away, with crystal-clear water for snorkelling. The other thing worth flagging: Key West is expensive, especially for accommodation, and it fills up in high season. With a bit of planning (booking the ferry early, getting around by bike or on the city's public transport, eating at Cuban places) you can enjoy it without going broke.
The island appears in European records with Juan Ponce de León's expedition in 1513, but it never had a permanent Spanish settlement. Sailors called it Cayo Hueso because of the human remains they found there, left by the Indigenous peoples who used it as a burial ground. In 1763, when Florida passed from Spain to Great Britain, the last Calusa were taken to Cuba. In 1815 the Spanish governor of Cuba granted the island to Juan Pablo Salas, who sold it twice: John W. Simonton closed the purchase in a Havana café in January 1822, and on 25 March that year Matthew C. Perry raised the US flag. In 1823 the Navy set up a base to fight piracy. In the 1830s, salvaging ships wrecked on the reef made it one of the richest cities in the country per capita. From 1868, Cuban exiles from the Ten Years' War built up a major cigar industry, and in 1886 a fire destroyed 18 factories and 614 homes. In 1898 the battleship Maine sailed from here to Havana. In 1912 Henry Flagler's Overseas Railroad arrived; the 1935 Labor Day hurricane destroyed it, and in 1938 the Overseas Highway opened on top of its bridges. Hemingway lived on the island from 1931 to 1939, and Truman spent 175 days at the Little White House between 1946 and 1952. In 1982, in protest against a border checkpoint on the highway, the city jokingly declared itself the 'Conch Republic', a celebration held every 23 April. In 2017 Hurricane Irma struck the Keys as a Category 4 storm.
Read the full history ↓The 'sunshine state': the land with the oldest European roots in the country, with St. Augustine; home of the Timucua, the Seminoles and the Everglades, of the tourism of Miami and Orlando, of Cape Canaveral and of a vibrant Latino culture.
Read the history of Florida →A local guide tells you in half an hour what no sign at the site will ever explain. We look ours up on Civitatis: guided in Spanish and booked online with no fuss. They have 16 activities in Key West. Three are below so you get the idea: tap any of them and they all open.
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Origins, formation and what the sources say.
The island we call Key West today was inhabited by Indigenous peoples of Florida, such as the Calusa and the Tequesta, long before the Europeans arrived. When Spanish explorers ran along the chain of keys in the 16th century, they named the southernmost island Cayo Hueso, that is, 'bone island', by tradition because they found human remains on it, possibly from old burials or from battles between tribes. From that Spanish expression comes, by phonetic adaptation, the present English name 'Key West'.
Through the colonial centuries the island stayed practically uninhabited by settlers, though it was known to sailors and fishermen. Florida was Spanish territory until 1821, when it passed to the United States. Shortly afterward, in 1822, an American businessman, John W. Simonton, bought the island, and the U.S. Navy took possession of it for its strategic value: Key West controlled the passage between the Gulf of Mexico and the Atlantic, one of the busiest sea routes of the era.
The official founding of the modern settlement dates to the 1820s. Its strategic position, at the gateway to the Straits of Florida and near Cuba, would shape its entire history, turning it into a military and commercial enclave and, in time, into one of the most singular places in the country.
Through the 19th century, Key West lived a period of remarkable prosperity thanks to a peculiar industry: wrecking, the salvaging of shipwrecked vessels. The treacherous reefs surrounding the Keys caused numerous wrecks, and the island's inhabitants specialized in rescuing grounded ships and recovering their cargo, a legal and highly lucrative activity that, so the story goes, made Key West the city with the highest per capita income in the United States in the mid-19th century.
Other industries added to that wealth. From the 1860s and 1870s on, Cuban tobacco workers arrived and set up cigar factories, turning Key West into a major center of Havana-cigar production (before many of those factories moved to Tampa). The island also prospered on sea-sponge fishing, another key part of its economy. The population grew with a mix of Bahamians, Cubans, Americans and others, which gave the island its cosmopolitan, Caribbean character.
The building of lighthouses —like the current Key West Lighthouse, rebuilt in 1848 after a hurricane— improved the safety of navigation and, paradoxically, gradually reduced the wrecks and, with them, the era of wrecking. Even so, Key West remained a prosperous port and the largest city in Florida for a good part of the 19th century, with splendid conch-style wooden houses that still define the look of its Old Town.
At the start of the 20th century, the magnate Henry Flagler took on a colossal project: extending his Florida East Coast railroad all the way to Key West, hopping from key to key over the sea. The 'Overseas Railroad' was completed in 1912 and linked the island to the mainland for the first time, an engineering feat considered the eighth wonder of the world in its day. The devastating Labor Day hurricane of 1935 destroyed much of the railroad; the present Overseas Highway (US-1), the road that today links the Keys through a succession of bridges, was later built along its route.
In the 1920s and 1930s, Key West drew writers and artists seduced by its light, its isolation and its unique atmosphere. The most famous was Ernest Hemingway, who lived there in the 1930s in the house that is a museum today, where he wrote part of his work and whose polydactyl feline descendants still inhabit the place. Other writers passed through the island as well, cementing its reputation as a creative refuge. The Great Depression hit Key West hard —the city went so far as to declare municipal bankruptcy in 1934— and the federal government, through the New Deal, actively promoted tourism as a strategy for economic recovery, laying the foundations of the industry that sustains the island today.
Through the 20th century, Key West reinvented itself as a tourist mecca, keeping its independent, tolerant and festive spirit, fed too by its role as a strategic naval base during the Second World War and the Cold War (it was crucial during the Cuban Missile Crisis in 1962, given how close it is to the island).
One of the most colorful episodes in Key West's recent history happened in 1982. Faced with a road and immigration checkpoint set up by the U.S. Border Patrol at the only land access to the Keys (supposedly to look for undocumented immigrants and drugs), which caused enormous traffic jams and badly damaged tourism, the mayor of Key West and a group of residents answered with humor and defiance: they declared the island's symbolic 'secession' as the Conch Republic, raised their own flag, named a 'prime minister' and, right afterward, 'surrendered' to the United States, asking for humanitarian aid as a defeated foreign country. The gesture, half political protest and half theatrical joke, achieved its aim: the border checkpoint was removed, and ever since the Conch Republic has been celebrated every year with a festival and remains an emblem of the island's rebellious, ironic character, with its motto 'We Seceded Where Others Failed'.
Since the late 20th century, Key West also established itself as one of the great LGBTQ+ destinations in the United States, with an open, well-established community and social scene dating from the 1970s and 1980s, largely tied to its bohemian tradition of tolerance. That openness, added to the literary legacy of Hemingway and other writers, the fame of its sunsets at Mallory Square and the boom in cruise ships calling at the island, finished shaping contemporary Key West: an economy centered almost entirely on tourism, receiving several million visitors a year.
Today Key West combines its inheritance of shipwrecks, cigars and literature with the challenges of a mass destination on a small, low-lying island: managing tourism, the cost of living that has shot up for its residents and its vulnerability to hurricanes and rising sea levels are the big issues of its present. Even so, it keeps intact the spirit summed up in its local philosophy, 'One Human Family', and remains, ninety miles north of Cuba, one of the most singular corners in all of the United States.
